N-[1-(5-fluoropentyl)-4-piperidinyl]-N-phenylpropanamide

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-[1-(5-fluoropentyl)-4-piperidinyl]-N-phenylpropanamide
• 英文别名: N[1-(5-[18F]fluoropentyl)-4-piperidinyl]-N-phenylpropanamide；N-[1-(5-fluoropentyl)piperidin-4-yl]-N-phenylpropanamide
• 化学式: C₁₉H₂₉FN₂O
• 分子量: 320.45
• InChiKey: WNSZJHLFZGQSLV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  23
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  23.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1-溴-5-氟戊烷 、 N-苯基-N-(4-哌啶)丙胺 混合盐酸 在 potassium carbonate 作用下， 以 四氢呋喃 为溶剂， 反应 5.33h， 以45.6%的产率得到N-[1-(5-fluoropentyl)-4-piperidinyl]-N-phenylpropanamide
  参考文献：
  名称：

  Syntheses, Biological Evaluation, and Molecular Modeling of ¹⁸F-Labeled 4-Anilidopiperidines as μ-Opioid Receptor Imaging Agents

  摘要：

  The synthesis, evaluation, and molecular modeling of a series of F-18-labeled 4-anilidopiperidines with high affinities for they-opioid receptor (mu-OR) are reported. On the basis of the high brain uptake and selective retention in brain regions that contain a high concentration of they-OR, combined with a good metabolic stability, [F-18]fluoro-pentyl carfentanil ([F-18]4) and 2-(+/-)[F-18]-fluoropropyl-sufentanil ([F-18]6) were selected as the lead compounds for further evaluation. The binding affinity to the human mu-OR was 0.74 and 0.13 nM for [F-18]4 and [F-18]6, respectively. In vitro autoradiography of [F-18]4 and [F-18]6 on rat brain sections produced patterns in accordance with the known distribution of mu-OR expression. Structure-activity relationships of the fluorinated compounds are discussed with respect to the interaction with an activated-state model of the mu-OR. Taken together, the in vivo and in vitro data indicate that [F-18]4 and [F-18]6 hold promise for studying they-opioid receptor in humans by means of positron emission tomography.

  DOI：

  10.1021/jm0507274

文献信息

• Syntheses, Biological Evaluation, and Molecular Modeling of ¹⁸F-Labeled 4-Anilidopiperidines as μ-Opioid Receptor Imaging Agents
  作者：Gjermund Henriksen、Stefan Platzer、János Marton、Andrea Hauser、Achim Berthele、Markus Schwaiger、Luciana Marinelli、Antonio Lavecchia、Ettore Novellino、Hans-Jürgen Wester

  DOI：10.1021/jm0507274

  日期：2005.12.1

  The synthesis, evaluation, and molecular modeling of a series of F-18-labeled 4-anilidopiperidines with high affinities for they-opioid receptor (mu-OR) are reported. On the basis of the high brain uptake and selective retention in brain regions that contain a high concentration of they-OR, combined with a good metabolic stability, [F-18]fluoro-pentyl carfentanil ([F-18]4) and 2-(+/-)[F-18]-fluoropropyl-sufentanil ([F-18]6) were selected as the lead compounds for further evaluation. The binding affinity to the human mu-OR was 0.74 and 0.13 nM for [F-18]4 and [F-18]6, respectively. In vitro autoradiography of [F-18]4 and [F-18]6 on rat brain sections produced patterns in accordance with the known distribution of mu-OR expression. Structure-activity relationships of the fluorinated compounds are discussed with respect to the interaction with an activated-state model of the mu-OR. Taken together, the in vivo and in vitro data indicate that [F-18]4 and [F-18]6 hold promise for studying they-opioid receptor in humans by means of positron emission tomography.